How Chicago Battled for Success With ‘Chicago Transit Authority’

Chicago is now known as the legendary “rock and roll band with horns,” but in the early going, they faced an uphill battle. Surprisingly, it wasn’t with the critics.

1969’s Chicago Transit Authority is a sprawling double LP of free form music that clocks in at close to 80 minutes of music — something which in the digital age, would be less shocking. On the edge of the ’70s, it was excessive, especially considering that it was the group’s debut album. But they ran into a different problem — radio programmers were balking at playing the band’s initial singles. “Questions 67 & 68” stalled at No. 71 on the Billboard Hot 100, while its follow-up, “Beginnings,” failed to make the charts.

“They literally said that because we hadn’t had a hit yet, they couldn’t play the song,” trumpet player Lee Loughnane, a co-founding member of the group, recalls now during a conversation on the UCR Podcast. “Wait a minute here, that’s the Catch 22 here. How are we going to have a hit if you don’t try it? The critics loved us, initially, with the first album. ‘These guys are way ahead of their time. What do they have for the second record?’ But AM radio wouldn’t play the singles.”

Listen to Chicago’s ‘Beginnings’

Frustrated, yet undeterred, the group kept their focus on road work. “We were playing schools and wherever else. We played everywhere across the country,” he remembers. “As we were writing the second album, we were rehearsing those songs on the road. It’s something that you hear on the Carnegie Hall [live album] and especially with the Kennedy Center performance. We were going to be recording the songs for [our fourth studio] album about a week after we finished that particular show. We hadn’t figured out who was going to sing the lead vocals and stuff like that. To do a major concert as we were still rehearsing songs, I’m going, ‘How did we have the stones to try to pull that off?’ But it was really the only time that we could work on the songs, because we were always gone. We were always working.”

READ MORE: How Chicago Continued to Evolve in the ’70s

Chicago & Friends: Live at 55, released in late November, offers a look at the history that they ultimately bottled on the Chicago Transit Authority album. Recorded across two concerts in Atlantic City in 2023, it documents the stunning star-studded performances that unfolded on stage each night. The group performed 35 songs at both shows, split into two sets, clocking in at more than two and a half hours. Aside from a few covers that were trimmed out, fans can now enjoy nearly everything that was performed.

Heavy focus is put on the songs from Chicago Transit Authority. “Beginnings,” “Questions 67 & 68” and “Does Anybody Really Know What Time it Is” and others from the album have remained set list staples. But the Atlantic City gigs also unearthed some true rarities, things like “Listen” and “Poem 58” that hadn’t been performed live by the group since the ’70s. Steve Vai, a noted fan of late Chicago guitarist Terry Kath, steps in to perform two songs, including “South California Purples,” which was being aired out for the first time since the beginning of the ’80s. Additional guests, including Robert Randolph and Christone “Kingfish” Ingram, further elevate the impact of the material from the band’s now-historic debut.

Listen to Chicago’s Performance of ‘South California Purples’ With Steve Vai

In a sense, the Atlantic City performances demonstrate how the songs have continued to evolve. That lines up well with how the group itself was changing in the early years prior to Chicago Transit Authority, a time period where they’d relocated from Chicago to California. “We actually had no idea what was going to happen. We just went out there thinking that hopefully something will happen,” Lougnane says. “We just kept playing the songs that we knew. And we were playing, you know, covers of Top 40 songs, We listened to the Vanilla Fudge, who were in fact, doing arrangements of other people’s hits that were already established, and they’d do a different arrangement of it. That’s where we we started doing the same thing, and that was our development. Once we got on record, we were [taking] different aspects of music and combining them all together in one song.”

READ MORE: When Chicago Got Meta on ’25 or 6 to 4′

According to Loughnane, there were no real sonic templates in mind when they went into the studio to record the songs for Chicago Transit Authority with producer James William Guercio. “I don’t know if we necessarily did it that way, other than have the songs rehearsed to the point where the writer would bring it in and then sort of turn it over to us,” he says. “As we played it, we would start thinking of ways of furthering the song along, and then by the time we got into the studio, we’d have the track pretty well together. We would record the brass parts at the same time, knowing full well that we were going to re record the brass, but it’s going to be the same notes, so it wouldn’t matter if you could hear the bleed in the background. [That] was going to be heard whether you liked it or not. So if the parts were the same, it wouldn’t matter at all.”

The ‘Experience’ of Opening for Jimi Hendrix

The group notched another important early milestone in 1969 when they were invited to open a series of concerts for the Jimi Hendrix Experience. Looking back now, the gigs are an example of how much the band still had to learn, but they also saw some positive signs.

“We went on first, obviously, and the audience was more interested in hearing Jimi, so there was a lot of, “Put Jimi on stage” chants, rather than listening to us,” Loughnane reflects. “But I think enough people recognized and enjoyed hearing what we were doing and thought, ‘These guys aren’t so bad.’ We were set up in this little tiny group up on stage. It was probably a 40-foot stage. We were used to [playing clubs], so we were already tight together. That’s the way we configured ourselves on the bigger stages when we first went out with Jimi Hendrix and Janis Joplin. So it had to look pretty [weird], ‘Why are these guys standing together like that so close?’ We didn’t know any other way of doing it at that point.”

Listen to Lee Loughnane on the ‘UCR Podcast’